Search Holiday Rentals in Pittsfield

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
11 Jan - 12 Jan
Tomorrow
12 Jan - 13 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Pittsfield holiday rentals

View from property
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.0 star property
Epsom
9.6 out of 10, Exceptional, (102 reviews)
"This was our second stay and it’s a 10/10 for a romantic getaway! "
United States
Caitlin
The price is 2.862.994 ₫
4.246.293 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Classic Apartment, Non Smoking | Private kitchen | Full-sized fridge, microwave, oven, stovetop
9 Lake Street

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is 3.703.506 ₫
6.440.686 ₫ total
includes taxes & fees
16 Jan - 17 Jan
9 Lake Street
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

10/10 Excellent
"Great"
Ryan 3-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday rentals for your stay in Pittsfield.

What’s there to see and do in Pittsfield?

Lily Lake and Suncook River are a couple of scenic spots to enjoy the outdoors, whereas Scenic Theatre is one of the cultural attractions. Other places in town to visit include Josiah Carpenter Library and Pittsfield Town Hall.

What’s a holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.